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photo of rolo cookie split in half with caramel in the center

Rolo Chocolate Crackle Cookies


Classic chocolate crackle cookies with a surprise caramel center.


  • 5 tablespoons unsalted butter, melted
  • 3/4 cup light brown sugar
  • 1 egg
  • 1 teaspoon vanilla
  • 3/4 cup flour
  • 1/3 cup unsweetened cocoa powder (I used Hershey’s)
  • 3/4 teaspoon baking powder
  • 1/3 cup confectioners’ sugar
  • 20 mini Rolos


  1. Preheat oven to 350°F. Line a cookie sheet with parchment paper or lightly spray with cooking spray.
  2. In a large bowl, mix the butter and sugar together. Add the egg and vanilla and continue mixing until well combined. Add the flour, cocoa powder, and baking powder. Mix until just combined. Allow the dough to chill in the fridge for 30 minutes.
  3. Pour the confectioners’ sugar into a small bowl. I find it’s easiest to roll the cookies with wet hands to keep the dough from sticking to my hands.
  4. Press one Rolo candy in the center of a generous tablespoon of cookie dough. Roll in your hands to cover the entire candy.
  5. Roll the cookie ball in the confectioner’s sugar and place on cookie sheet (space cookies about 2 inches apart).
  6. Bake for 10 minutes, or until the cookies crack on top. Carefully transfer the cookies to a cooling rack. Once cooled, store in an airtight container.


Recipe adapted from Glamour Magazine

  • Prep Time: 50 minutes
  • Cook Time: 20 minutes
  • Category: Desserts
  • Method: Bake
  • Cuisine: American


  • Serving Size: 2 cookies
  • Calories: 214
  • Sugar: 22.3g
  • Sodium: 35mg
  • Fat: 9.2g
  • Saturated Fat: 5.7g
  • Unsaturated Fat: 2.6g
  • Trans Fat: 0g
  • Carbohydrates: 32.1g
  • Fiber: 1.2g
  • Protein: 2.8g
  • Cholesterol: 35.3mg

Keywords: chocolate crackle cookies, rolo cookies